Cosmetic use of Bis(resorcinyl)triazine derivatives

Details Cosmetic use of Bis(resorcinyl)triazine derivatives Cosmetic use of Bis(resorcinyl)triazine derivatives

2000-02-17

2001-04-24

Dodson, Shelley A. (Department: 1616)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S060000, C424S400000, C424S401000, C514S241000

Reexamination Certificate

active

06221342

ABSTRACT:

The present invention relates to the use of selected bis(resorcinyl)triazine derivatives for protecting human and animal skin and hair from the damaging effect of UV radiation and to a cosmetic formulation comprising these bis(resorcinyl)triazine derivatives.
The bis(resorcinyl)triazines used according to this invention correspond to formula (1)
wherein
R
1
and R
2
are each independently of the other hydrogen; branched C
5
-C
18
alkyl; C
2
-C
18
alkenyl; a radical of formula —CH
2
—CH(—OH)—CH
2
—O—T
1
; a radical of formula (1a)
 or a radical of formula (1b)
R
3
and R
4
are each independently of the other hydrogen or C
1
-C
5
alkyl;
R
5
is hydroxy; C
1
-C
5
alkoxy which is unsubstituted or substituted by one or several OH groups; amino; mono or di-C
1
-C
5
alkylamino; M; a radical of formula
R
6
is a direct bond; a straight-chain or branched C
1
-C
4
alkylene radical or a radical of formula
R
7
, R
8
and R
9
are each independently of one another C
1
-C
18
alkyl; C
1
-C
18
alkoxy or a radical of formula (1i)
R
10
, R
11
and R
12
are each independently of one another C
1
-C
14
alkyl which is unsubsttuted or substituted by one or several OH groups;
R
13
is hydrogen; M; C
1
-C
5
alkyl; or a radical of formula —(CH
2
)
m
2
—O—T
1
;
R
14
is C
1
-C
5
alkyl;
M is a metal cation;
T
1
is hydrogen; or C
1
-C
8
alkyl;
m
1
is 1 to3 ;
m
2
is2 to 14; and
p
1
is 0; or a number from 1 to 5.
C
1
-C
5
Alkyl, C
1
-C
8
alkyl and C
1
-C
18
alkyl are straight-chain or branched allcyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl.
C
1
-C
5
Alkoxy and C
1
-C
18
alkoxy are straight-chain or branched alkoxy radicals, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butyloxy, sec-butyloxy, tert-butyloxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy or octadecyloxy.
C
2
-C
18
Alkenyl is, for example, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, iso-dodecenyl, n-dodec-2-enyl or n-octadec-4-enyl.
Examples-of mono- or di-C
1
-C
5
alkylamino are methylamino, ethylamino, propylamino, n-butylamino, sec-butylamino, tert-butylamino, pentylamino, dimethylamino, diethylamino; dipropylamino; dibutylamino or methylethylamino.
Examples of metal cations are the lithium, potassium, sodium, calcium, magnesium, copper or zinc ion.
According to this invention, it is preferred to use bis(resorcinyl) compounds of formula (2)
wherein
R
15
and R
16
are each independently of the other branched C
5
-C
18
alkyl; or
—CH
2
—CH(—OH)—CH
2
—O—T
1
;
R
17
and R
18
are each independently of the other hydrogen or C
1
-C
5
alkyl; and
T
1
is hydrogen; or C
1
-C
5
alkyl.
Preeminently interesting compounds are those of formula (2), wherein
R15 and R
16
are each independently of the other branched C
5
-C
18
alkyl or —CH
2
—CH(—OH)—CH
2
—O—T
1
;
R
17
and R
18
are hydrogen; and
T
1
is hydrogen; or C
1
-C
5
alkyl; and in particular those compounds of formula (2), wherein
R
15
and R
16
are each independently of the other branched C
5
-
18
alkyl; and
R
17
and R
18
are hydrogen.
Very particularly preferred are those triazine compounds of formula (2), wherein R
15
and R
16
have the same meaning.
Other triazine derivatives which may be used according to this invention are those corresponding to formula (3)
wherein
R
19
and R
20
are each independently of the other the radical of formula
and
R
21
, R
22
R
23
are each independently of one another hydrogen; or C
1
-C
10
alkyl.
Examples to be mentioned of compounds of formula (1) are:
2-(4′-methylphenyl)4,6-bis(2′-hydroxy-4′-n-octyloxyphenyl)1,3,5-triazine;
2-(2′,4′-dimethylphenyl)-4,6-bis(2′-hydroxy-4′-n-octyloxyphenyl)-1,3,5-triazine;
2-phenyl-4,6-bis(2′-hydroxy-4′-n-octyloxyphenyl)-1,3,5-triazine;
2-phenyl-4,6-bis(2′-hydroxy-4′-n-octyloxyphenyl)-1,3,5-triazine;
2-phenyl-4-{[4-(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy]phenyl }-6-(4-methoxyphenyl)-1,3,5-triazine;
2-(4′-methylphenyl)-4,6-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-1,3,5-triazine;
2-(2′,4′-dimethylphenyl)-4,6-bis{[4 -(2-ethylhexyloxy)-2-hydroxy]phenyl}-1,3,5-triazine;
2-phenyl-4,6-bis{[4-(2-ethylhexyloxy)-2-hydroxy]lphenyl}-1,3,5-triazine;
2-phenyl-4,6-bis{[4-(tris(trimethysiloxysilylpropyloxy)-2-hydroxy]phenyl}-1,3,5-triazine;
2-phenyl-4,6-bis{[4-(2″methylpropenyloxy)-2-hydroxy]phenyl}-1,3,5-triazine;
2-phenyl-4,6-bis{[4-(3(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy]phenyl}-1,3,5-triazine; or
2-phenyl,4,6-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-1,3,5-triazine.
Other examples of triazine derivatives are listed in Table 1:
TABLE 1

R
a
R
b
R
c
H

CH
3

H

CH
3

H
—OH
—OH
CH
3
—OH
—OH
H
—OH
—OH
H
—OM
—OM
M = alkali metal, alkaline earth metal,
M = alkali metal, alkaline earth metal, Cu,
Cu, Zn, Mg
Zn, Mg
CH
3
—OM
—OM
M = alkali metal, alkaline earth metal,
M = alkali metal, alkaline earth metal, Cu,
Cu, Zn, Mg
Zn, Mg
H
O
−+
N(CH
2
CH
2
OH)
3
O
−+
N(CH
2
CH
2
OH)
3
CH
3
O
−+
N(CH
2
CH
2
OH)
3
O
−+
N(CH
2
CH
2
OH)
3

H
n = 2-14
n = 2-14

CH
3
n = 2-14
n = 2-14

H

CH
3

H

CH
3

H

CH
3

H

CH
3
The bis(resorcinyl)triazines which may be used in accordance with this invention can be prepared in different manner, for example using aromatic nitrite compounds as starting compounds. The dichlorotriazine compound of formula
can be prepafor example, by reacting benzonitrile with dicyandiamide to the diaminotriazine compound which is subsequently saponified to the dihydroxytriazine (tautomer=dione) and then converted to the dichlorotriazine compound of formula (1k) with thionyl chloride. The two resorcinol groups are then introduced in commonly known manner by Friedel-Crafts acylation of resorcinol in the presence of a Lewis acid, preferably aluminium chloride. In the third step, the free hydroxyl groups in p-position are etherified, depending on the meaning of R
1
and R
2
in the compound of formula (1) by alkylation or acid-catalysed addition of glycidyl ethers.
Other processes for the preparation of the triazine derivatives which can be used in accordance with this invention are descnbed in EP-A-0,775,698.
The bis(resorcinyl)triazine compounds of formula (1) used according to this invention are particularly suitable as UV filters, i.e. for protecting ultraviolet-sensitive organic materials, in particular human and animal skin and hair, from the harmful effect of UV radiation. These compounds are, in particular, very powerful UVA absorbers with fractions in the UVB range and can be produced at low cost Accordingly, these compounds are suitable for use as light stabilisers in cosmetic, pharmaceutical and veterinary compositions. They can be used in dissolved as well as in micronised state.
Accordingly, this invention also relates to a cosmetic formulation, which comprises at least one compound of formula (1) as well as cosmetically compatible carriers or auxiliaries.
For cosmetic use, the light stabilisers of this invention usually have an average particle size in the range from 0.02 to 2, preferably from 0.05 to 1.5 and, most preferably, from 0.1 to 1.0 m. The insoluble UV absorbers used according to this invention can be brought to the desired particle size by customary methods, for example by grinding e.g. with a jet, ball, vibratory or hammer mill. Grinding is preferably carried out in the presence of 0.1 to 30 by weight, preferably of 0.5 to 15% by weight, based on the UV absorber, of a grinding aid such as an alkylated vinylpy

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